


A Day I Can't Forget

by whosthatpokaimon



Category: Gotham (TV)
Genre: Anal Fingering, Anal Sex, Animalistic, Arkham Asylum, Autoerotic Asphyxiation, Begging, Biting, Canon Compliant, Dirty Talk, Dissociative Identity Disorder, Gay Sex, Gratuitous Smut, Hair-pulling, Handcuffs, Light BDSM, Loss of Virginity, M/M, Orgasm Delay/Denial, Praise Kink, Shameless Smut, season 4
Language: English
Status: Completed
Published: 2020-09-23
Updated: 2020-09-23
Packaged: 2021-03-07 17:47:59
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,877
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26611690
Author URL: https://archiveofourown.org/users/whosthatpokaimon/pseuds/whosthatpokaimon
Summary: Edward arrived at Arkham to sign papers for Lee, but he got a little... Distracted upon seeing Oswald as a part of him he didn't know still existed resurfaced with new plans.Title from Lover Is A Day - Cuco
Relationships: Oswald Cobblepot/Edward Nygma
Comments: 1
Kudos: 63





	A Day I Can't Forget

**Author's Note:**

> this is just some filthy porn to apologize for my last piece, enjoy the kinky

_“Riddler...”_

When Ed returned to rescue Oswald from Arkham, this wasn’t quite what he expected. His face had been so forcefully grabbed that he was afraid Ed was just going to try to kill him again. Then, his grip softened, breath evening out, and Oswald’s brain short-circuited. Their lips were so close, his head was angled so perfectly that he only needed a gentle push forward and their lips would be locked together. He could see the switch in Ed’s - _The Riddler’s -_ eyes, the darkness circling them like the eye of a storm and the way his expression shifted from anger to, dare he say it, _hunger._ He still looked so attractive in his disheveled state; hair falling in his face, glasses askew, and suit jacket pulled open by Oswald’s hands.

Riddler skirted his thumb across Oswald’s bottom lip and Oswald froze when persistent lips replaced the thumb as if waiting for confirmation that this was real. That Riddler wanted him just as much as he wanted Riddler. Eyes wide, he pulled back and frantically searched his expression for any uncertainty. Riddler only smiled back, a genuine but borderline sinister smile.

“I see your confusion. Don’t worry, I’ve wanted you for longer than you could imagine. Edward was too stubborn and he stood in my way, and now, I can finally have you,” his voice dropped to a low growl at the end of his statement and Oswald’s cock twitched excitedly in his pants. All worries faded, Oswald pulled him back in, gripping tightly to the lapels of his jacket. Oswald’s eyelids fluttered shut as Riddler’s hand traveled to the back of his head to gently tug at his hair and hold him in place. Oswald parted his lips and moaned into the kiss, feeling Riddler’s tongue breach his mouth at the opportunity. He bucked his hips forward desperately, his erection imprisoned in his pants and aching for friction.

Riddler pulled away and Oswald whined from the lack of contact before Riddler placed a pointer finger over his lips, “Ah ah ah, don’t you think we should be somewhere more private?”

Oswald hesitated before nodding, not wanting to admit that he got so lost in the moment he forgot where they were. Riddler grinned, Oswald wondering how it would feel to have those teeth sink into his neck. The thought only heightened his arousal, impatiently following Riddler to a secluded cell. The screams of the insane were muffled against the walls that seemed thicker in this cell. He sat Oswald down onto the bed and gave him a kiss that was way too short for Oswald’s liking.

“Stay right here, my little bird, I’ll be right back,” he purred before spinning on his heel and exiting the cell, leaving Oswald horny and pouting on the bed. No more than three minutes later, Riddler returned wearing an Arkham uniform. Oswald looked at him with a confused expression and Riddler let out a laugh.

“Just indulging in one of my fantasies,” He approached Oswald and he could see the outline of his erection through the thin material, “I would think about you when I was in this place. Every night, just me and my thoughts, they always came back to you.”

He pushed Oswald down onto the bed and pinned his hands above his head, making Oswald gasp lightly. Riddler knelt between Oswald’s legs and leaned forward. He could feel Riddler’s hot breath against the shell of his ear.

“I’d think about us, in this exact position, fucking you so hard that you begged me to stop…”

He shifted so he could hold both of Oswald’s wrists in one hand, the other trailing down to pull open the buttons of Oswald’s shirt.

“I’d think about shoving your face into the mattress as I watched your ass bounce with every thrust…”

His words only made Oswald want more as his hips bucked and he moaned out rather loudly when their cocks rubbed together at the moment. Riddler let out a deep groan, muttering a “fuck” into Oswald’s ear.

“I’d imagine scenarios where it was the other way around, too, but I can save those for another time,” his hand pushed open Oswald’s shirt to tweak one of his nipples and made a steady rhythm with his hips, grinding against Oswald, “Right now, I’m the one in control.”

It was humiliating to admit, but he loved being at the other man’s mercy. Completely powerless as The Riddler took what he wanted from him. It was intoxicatingly arousing.

Oswald’s back arched from the sensation of Riddler rolling and pinching his nipple, alternating to give equal attention to both. Riddler leaned down to kiss him with even more hunger as his hand slid lower and beneath his waistband. Oswald panics and pulls away from the kiss to speak up, “Riddler, wait-!”

“Hmm?”

“I don’t have any lubricant…”

“Good thing I always come prepared,” he purred into Oswald’s ear, waving around a bottle he pulled from the pocket in his pants. Oswald gaped and looked between him and the bottle.

“How did Ed let you take that with you?”

“He always keeps a bottle on hand. I’m just lucky that he forgot it was with us,” he smirked, “I also have this.”

Riddler removed a pair of police handcuffs from his pocket as well. Oswald didn’t protest as Riddler took his wrists and clicked the handcuffs closed, binding them to the bed frame, “There, that’s better.”

Oswald smirked and nibbled his lower lip as Riddler trailed his hands down his torso. Riddler stopped every now and then to kiss and suck hickeys into Oswald’s pale skin. The sensation made Oswald shudder. Once Riddler got to his waistband, he was teasingly slow in the removal of his pants. Oswald bucked his hips, seeking friction and finding it in Riddler’s hand as he palmed him through his boxers. He didn’t bother restricting his moans since Riddler brought himself back up to swallow the noises in a hungry kiss anyways.

After a few moments, Riddler tugged off his underwear and dragged a lubed finger across Oswald's hole, dipping the tip inside slightly. Oswald tried to push his ass down to fuck himself on Riddler’s fingers, relishing in the feeling of finally having the man’s fingers inside of him, but Riddler used his other hand to hold down his hips.

“Patience, I want to take my time and enjoy this,” Riddler pumped his finger slowly in and out and Oswald barely felt the sting until a second finger was added. He groaned at the stretch but relaxed his muscles to the best of his ability. Riddler chuckled, “I _knew_ it. You’re a virgin, aren’t you, Oswald?”

Oswald nodded, trying to hide his reddened face in his arm, hoping to hide the embarrassment, “I-I wanted to save myself for you…”

“That’s okay, I feel honored to be popping The Penguin’s cherry. You’re doing so good for me,” Riddler praised and it made Oswald’s heart flutter. Once the pain subsided, he nodded to let Riddler know that he could add a third finger.

He should’ve waited a bit longer. Riddler’s third finger was almost unbearable. He whimpered and tried to relax more, but it was getting increasingly difficult.

“Shh, it’s okay, just relax. You’re doing great,” Riddler softened his voice, something Oswald hoped wouldn’t last long. He hated to admit it, but he enjoyed the praise, but hearing it from Riddler felt strange.

He paid that thought no mind as he finally managed to relax, shifting his hips in time with the other male’s fingers. They crooked inside of him and Oswald gasped out a choked moan as a bolt of pleasure struck him. He started to grow impatient, wanting to feel it deeper, huffing out another moan, “I’m ready, Riddler, just fuck me, please.”

“Your wish is my command,” He responded, removing his fingers to pull down his pants and spurt a generous amount of lube onto his shaft. Oswald didn’t know Riddler liked to go commando…

The tip of Riddler’s cock pushed its way into Oswald, earning a hearty groan from both men. It stung, but the extensive prep helped tone down the pain. Soon enough, Riddler was completely buried inside of him and Oswald had to take a moment to recuperate. Riddler waited patiently, placing kisses down his neck.

Once he relaxed into the feeling, he shifted his hips and moaned at the movement. Riddler pushed and pulled slowly, making sure he didn’t hurt Oswald. He appreciated the sentiment, but he didn’t have the patience for this pace. His wrists chafed against the handcuffs. It wasn’t painful yet, but it was right on the edge.

“Faster…” Oswald muttered. Riddler complied without question, tugging at Oswald’s hair as he increased his pace and bit into his neck. Oswald moaned loudly into the otherwise quiet cell. Riddler was hitting his prostate with each thrust now and it made Oswald arch his back as he felt a pressure in his gut, signaling his release. He knew it was coming soon, but he didn’t care.

“Fuck, ah, don’t stop, don’t stop,” he cried out. The pressure was growing tighter and tighter until…

Riddler stopped moving. Oswald whined as his orgasm slipped away from him, “P-Please…”

Riddler continued to move, slow enough for Oswald’s release to be held back, but fast enough to where it wouldn’t slip away completely. Like pleasure limbo. He curled his fingers around Oswald’s neck gently as he purred, “Please what?”

“Please let me cum…”

“Try again,” He stopped moving again as Oswald tried to shift his hips to create some semblance of friction a _nywhere,_ but Riddler kept a good hold of Oswald’s hips with his own. The fingers on his neck tightened, “Who are you asking?”

“ _Riddler,_ p-please, please let me c-cum!” Oswald sobbed. He couldn’t afford to lose momentum, not now. Not when his orgasm was dying down.

“Good boy…” Riddler _growled_ before he really picked up the pace, one hand clasped tightly around Oswald’s neck as the other one stroked him in time with his thrusts. He leaned forward to sink his teeth into the skin on Oswald’s shoulder.

Oswald felt like he was going to pass out. His vision was getting blurry and he was seeing stars as the buildup returned with even greater vigor. His jaw went slack and his eyelids fluttered, whatever moan he made being reduced to a whimper from the pressure on his throat, as he finally came. Riddler let go of his neck with his own loud shout, the removal of the pressure allowing Oswald to scream at such a volume that he was sure they would be heard from the other end of the wing. He felt Riddler's cock pulse and release inside of him, making his legs quake.

They sat like that for a moment before Riddler pulled out, watching as his release dripped from Oswald with a grin. He glanced at Oswald as he pulled his pants back up, who was still trying to catch his breath. He undid the handcuffs and Oswald readjusted his clothing. Riddler leaned forward to kiss him softly, a gesture that made Oswald feel fuzzy inside. They were both left smiling as they pulled away.

“Shall we get to work?”

**Author's Note:**

> 3 fics in as many days??? yall are getting spoiled smh


End file.
